Methanol → HCID 22242804, compound

To a solution of 1-(4-carbamoyl-1,3-thiazol-2-yl)-4-hydroxypiperidine (1.93 g, 8.49 mmol) (obtained as described in Reference Example 15(2)) in methylene chloride (100 ml) were added methanesulfonyl chloride (10.0 ml, 129 mmol) and triethylamine (18.0 ml, 129 mmol) in an ice bath. After stirring the mixture in the ice bath for 10 minutes, the mixture was stirred at room temperature for 24 hours. After checking the completion of the reaction, methanol was added to the reaction mixture in an ice bath and the resulting mixture was stirred at room temperature for 30 minutes. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (10:1) as the eluant to afford 1-(4-carbamoyl-1,3-thiazol-2-yl)-4-methanesulfonyloxypiperidine (1.59 g, yield 61%) as a pale yellow solid.

1. additionwas added to the reaction mixture in an ice bath
2. stirringthe resulting mixture was stirred at room temperature for 30 minutes
3. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
4. washThe organic layer was washed with saturated aqueous sodium chloride solution
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by chromatography on a silica gel column

ORD record

ord-f2d387997c1e4d84962cf19cbaa8a2d8

Source dataset

uspto-grants-2006_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07001897B2